Preheat the oven to 375 F. Line 2 baking sheets with parchment paper.
Peel the butternut squash, then halve it. Scrape out and discard the seeds, then cut the flesh into ¾-inch chunks.
Whisk together ½ tablespoon of olive oil, honey, and ¼ teaspoon salt in a small bowl.
Add pumpkin seeds to the bowl and stir until well-coated.
Spread pumpkin seeds in a thin layer onto one of the parchment-lined baking sheets.
Put in oven and bake for 8 to 10 minutes, until glazed and toasted. Remove and set aside to cool, then break into pieces.
Increase oven temperature to 425 degrees Fahrenheit.
Add butternut squash pieces to second lined baking sheet, and toss with remaining tablespoon of olive oil, remaining ¼ teaspoon of salt, and black pepper.
Roast the squash for 20 minutes, until tender and beginning to brown.
While the squash is roasting, whisk the sherry vinegar, mustard, and honey in a small bowl. Then, slowly add olive oil, whisking constantly. Season to taste with salt and pepper, then set aside until ready to serve.
When squash is done, remove it from the oven and let it cool.
To serve the salad, add baby kale to a large salad bowl and toss with a few tablespoons of the dressing.
Top with roasted butternut squash, candied pumpkin seeds, crumbled goat cheese, and pomegranate seeds.